Keeping Alison company

December 24th, 2008

Do you want to read something real? How about a real diary where a guy shares his experiences of fucking a mature, married woman, he goes into a lot of detail and I am sure you want to know all of them…

We extend our thanks to the author JackTheMan.

Well where do I start. Alison is my mom’s friend. She’s 45, married. Being a mature woman, and also a mother, it’s a given that her breasts haven’t been helped any by gravity, but don’t let this put you off. She’s around 5ft 7, she has long legs and a long torso. Her tummy has a fat ring around it, but its attractive in its own right and her butt is complemented by it, creating more definition for those mature peachy butt cheeks. Defining her profile are those breasts: at 28B they are perfect, sagging significantly but still retaining a gorgeous bell drooping towards her nipples.

I know her fairly well, our two families having been friends for years. As I was maturing through puberty, I often twigged onto the most subtle of hints that she was turned on by my developing masculinity. She has a naturally bubbly and sexy personality, but doesn’t flaunt it – naturally as she is a mother and married. A number of times when giving her and my parents a lift after a night out she has dropped some more significant hints to her attraction towards me: things like a long kiss on the cheek, an innocent stroke of my crotch after a tight hug, and joking about being alone with a ‘young man’ in a car in the middle of the night.

Anyway. My parents own a flat in the city and I got a phone call to say that Alison had a job interview the next day and was going to be staying in the flat that night. So! My chance to make a move I thought.

Arriving at the flat unannounced, I opened the door and Alison greeted me. I told her I had no idea she was here and made up some crap about my shower being broken and needing to use the shower in the flat. She giggled and said ‘want me to scrub your back?’. I replied with a wink and said ‘maybe later’. So I had a shower, got out and wrapped a towel around by waist, walked into the lounge to see Alison and ‘accidently’ drop my towel to expose my throbbing erection.

She said ‘oh hi Jack’ and I said ‘hi Alison you don’t mind if I dry my hair here do you?’ To which she replied ‘not at all’. I bent over to pick up my comb and secretly loosened my towel, walked over innocently in front of Alison and as she looked up to make conversation when ‘oops!’ my towel dropped and out popped my rock-hard cock.

She gasped and froze, not looking away, but staring hypnotically at my throbbing shaft. I said ‘I know you want this Alison’. She softly said ‘yes, but I’m a married woman, and I’m old enough to be your mother!’. I just stared at her, she crossed her legs and her breathing got heavier. I said ‘Well, why don’t you just close your eyes for me?’ she did. I slowly pushed the head of my cock up to her lips and she instinctively opened her mouth and took the whole thing into her mouth and down her throat, then pulled it out of her mouth and said, ‘its not fair if only you gets naked’. She stood up and stripped right in front of me, until it was only her bra and panties left on. She said ‘If I take these off you have to promise that this whole thing is a secret’ to which I said ‘absolutely Alison’.

Taking off her panties, I saw for the first time my mature fantasies hairy pussy. She then progressed to let free her gorgeous bellowing plump saggy breasts, to which I then put my arms around her and said ‘I wanted you for so long, to put my young cock inside your mature body and give it intense pleasure’. She replied I’ve had so many moments whilst having sex with my husband that I had to force myself to not think of fucking you because I would always cum too soon’. I held her hand, kissed her passionately, then lead her to the bedroom.

‘I want this to be complete, can we fuck without a condom?’ I said.

And as she took off her wedding ring she said ‘I wouldn’t have it any other way Jack, I want your seed inside me so bad’.

Laying her on the bed, I climbed on top of her. Staring into her eyes, I slowly penetrated that soft, bulging, wet, hairy old pussy. As she moaned softly, she squealed ‘I love you Jack’.

After a soft, slow, passionate fuck, we moved onto more fast and hard fucking. Having her straddling me, riding me like a pro, I finally had the hot mom of my dreams consumed by my young 6 inch dick. Just imagine her soft, smooth, saggy, bouncy breasts with her big round nipples jiggling around her chest as she squealed ‘god! I love this young dick!’

She came. I held her tight. ‘You don’t have any regrets do you Alison?’ to which she stopped her heavy breathing, kissed me and said ‘don’t cum until I tell you, I want this all night long, I love you Jack’.

We fucked 6 times, I made her cum around 8 times and orgasm twice. We then spent half an hour cuddling. She kissed me so passionately saying ‘promise me that there will be more nights like this’ to which I said ‘you now own my cock and every drip of sperm that is in my balls Alison’. She smiled.
She said ‘I want your seed inside my pussy’, I said ‘not until I’ve taken your ass’. She giggled saying I’ve never been fucked up the ass’. I got her to bend over and said I’m gonna take your anal virginity Alison.

I used her dripping pussy to lube up my shaft and her ass. Slowly penetrating her anus, feeling the intense grip of her anal muscles grip my shaft and my dear Alison moan deeply. She squealed ‘I love you jack, I’m your slut’. I said ‘I love you too Alison’, I then started gradually humping her virgin ass hole faster and deeper, constantly rubbing her bulging clit until she felt what it was like to cum with a big young cock up her ass.

After she got her breath back, she straddled me and said, now it’s your turn sweety. It was like she was possessed, riding my young cock like there was no tomorrow. She was screaming my name ‘Jack!Jack! ohhhh Jack! I want your cum!’ how could I refuse!haha. Iv never ejaculated so fucking hard in my life. As I began to cum, she dropped onto my cock, tightening her pussy around my shaft and rocking back and forward with her hips. She then lay on her back and watched the hot sperm drip out of her gorgeous puffy red mother hole.

I pulled her ontop of me, told her I love her and held her tight. She said I’ve wanted this for so long, I finally got your seed inside me Jack. I love you.’

We slept long into the next morning, then did it all again, and of course my sweet mature woman got a fresh load of sperm inside her hot married pussy.

Part 2

It has been 4 months since this first fuck. We still meet about twice a month and are deeply in love. We’ve avoided pregnancy thanks to the morning after pill because there is no better way to make love than to be covered in each other’s cum.

Part 3

I thought I’d continue writing, it’s been a few months.

So, it’s the 6 month anniversary of our first fuck. We met at the flat on Saturday, and it felt like my cock wasn’t out of her body until Monday morning. She had bought new sets of underwear and some awesome push-up bras that made her breasts look amazing.

Now, don’t get me wrong, I like fucking girls my age, but the best sex I’ve had has been with Alison -inside her mature pussy. Imagine you were watching her ride me, stand back and look at the profile of our body’s moving in motion with each other: her hips bucking and my crotch thrusting, her breasts bouncing and my hands clutching her butt cheeks, listen to her moan and notice my smile, see the cum dripping down my balls and me sucking her big round nipples. Sex with a mature women is the best, its more intimate, it lasts longer and its so much naughtier because she’s married.

We both got each other gifts for the anniversary. I got Alison anal beads and she got me a flesh tight pussy simulator. She said that its so I can feel a pussy around my shaft when she isn’t there to fuck me! What an awesome girl! I love her.

Part 4

It’s been a while now since we’ve had the chance to meet and be intimate. She’s been busy working and I’ve been studying. We met last night, but she was in a really bad mood, something to do with work. She stayed ontop all night! Working out her anger and frustration. It was like she was in a trance, ruthlessly fucking through the night. My cock felt so raw by the time she was done, it kinda hurt, but I’d never do anything to jeopardise our relationship. When she fell asleep I went to the kitchen to wrap my throbbing manhood in some ice. My cock has had a good few work-outs in its time, but never that ruthless.

In the morning, Alison woke me, kissing me and saying she was sorry for the last night, she realised that she was overdoing it, we just hugged and said no more. She said that I could do one sick fantasy and she would let me no matter how painful or sick it was, she was getting turned on and so was i.
I let her go back to sleep, and then I started fucking her ass hole and choking her. She got so turned on by being dominated, she had a massive orgasm and squirted everywhere, It was sooo good. We just spent the rest of the morning cuddling.

Part 5

Well, it’s getting increasingly difficult to meet, Alison thinks her husband is getting suspicious that she is spending nights away. So we decided to stop spending nights away with each other so that we didn’t get found out – I’d hate to imagine what hell would break loose if we did get found out. We agreed to take a break in the relationship, which killed me inside but in the long run could save our relationship.

Two weeks passed and I desperately needed to see her. I phoned her and told her to drive to the woods near our town. When she arrived she got out of her car and hugged me so tight and kissed me so passionately and said ‘Babe, I love you so much. You’ve been so good during this tricky time. I’v missed you so much’. I said I couldn’t stop thinking about her and I needed to make love with her. She said ‘well, my husband is at football practice with the friends, and I need your cock so bad sweety. I’v got a blanket in the car, I need you inside me.’

We got the blanket out, spread it on the ground. Alison got her breasts out and we both got naked from the waist down. She lay down and I slowly got on top of her and penetrated my mature loves pussy. We held still and kissed for a good 5 minutes before we got going, it was amazing to feel her pussy grip around my young shaft deep inside her mature pussy, it was so intimate.

We fucked only once, mainly because anyone could have stumbled upon us and also her husband was due back at their house within the hour. When I came inside her, she started to cry.

I pulled out and got her to lay on top of me and cuddled her and asked her what was wrong. She said ‘I just miss you so much and I feel so bad that I’m not showing you how much I love you Jack.’

I kissed her, wiped away her tears and said ‘Alison, I love you no matter what hunny. I know things are difficult just now, but it will get better. And I know how much you love me, you wouldn’t take these risks to have an affair with me if you didn’t love me. You mean so much to me Alison’.

She smiled and then kissed me, then snuggled up to me for a cuddle. After a lil while we got dressed, kissed goodbye and then left.

Since that day, things are looking more promising for us to have our nights away again, we met in the woods to arrange a night to meet and my darling mature married mother girlfriend was smiling which just melted my heart. She gave me a quick blow-job before she had to get back home.

Part 6

So, finally back in each others arms. She was in the mood for some really slow passionate love making tonight, so I was gonna give it to her – my gorgeous mature woman. It felt to good to hold her in my arms again, to gently caress her big round nipples and slowly kiss her lips. Alison went to the bathroom to put on some make-up, she said she wanted to look her best for her boy. So I just sat on the bed an thought to myself ‘I cant believe that im living the dream, of every young guy, I actually get to make love to a mature woman – not only is she married, she has offsprings, but she is old enough to be my mom. To have her old hairy pussy grip onto my young shaft, to make a mature mother cum onto my groin and feel her body shudder because of what im doing to her, its so amazing.’

After a few intense passionate orgasms after a long build up of slow and gentle thrusting, we settled into eachothers arms and snuggled up together. Alison asked me ‘would you have fucked me if I was actually your mother Jack?’ I said ‘well, I wouldn’t have sex with my real mom because it grosses me out having incest sex with a fat not very attractive woman, but if you were my mom Alison, id be so tempted to have incest sex with you, and if u didn’t want to have sex with your son then I could see myself getting so horny id need to fuck you to quench my lust.’ Alison said ‘Oh my, your such a naughty boy Jack, and that’s why I love you hunny. Id let u fuck me anyday sweety hehe.’

In the morning, we had a shower together, but Alison looked uncomfortable. I asked her if she was ok. She said ‘recently iv been feeling so guilty that iv been cheating on my husband, I mean I love him, but I love you too Jack and I cant give up our relationship.’ I hugged her and said ‘Alison, I love you, u know that neither of us mean any harm, we are only doing this because we love each other.

Everything will be ok hunny.’ She smiled, telling me I always knew just the right thing to say and make her feel better. I gave her a back rub to relax her before she squatted down and gently sucked my cock till I came in her mouth.

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6 Responses to “Keeping Alison company”

  1. Colin Says:

    wow. what an intense story! i was totally blown away, literally (if you know what i mean)
    Id give anything to be in ‘Jack’s’ place!

  2. angie Says:

    The same scenario did happen to me once lately.And I did really enjoy myself with this young guy-24 years younger than me.But I dont think he would want it again with me as I supposed that he would just wanna know what and how a full-course sex is .I am and really hoping to look forward to have it one more time with him.

  3. cougar 307 Says:

    players only love when their playing, the husband might already know its not when the other partly notice a chance in anyone. thats nature,if long is that strong let the husband, or is the dick that good the trouble with stop is to not not start

  4. loverofpussy Says:

    this story makes me wana masturbate HARD! i get fucking horny evrytime i read a story.cant i be in such a story?

  5. daddyo Says:

    Fanatastic

  6. hippymarty Says:

    this is the kind of sex that i like


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